Evidence receipt / uncertainty
Published · transcript-backedJessica Fain: uncertainty
22 Mar 2026 Lenny's Podcast The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
“Now more than ever, that is not possible. And so one trick that I learned, especially working with engineers who often have a very, very high desire for certainty, is to say, "I don't know the answer right now.”
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Everything needed to verify it.
- Speaker
- Jessica Fain
- Attribution
- Verified speaker
- Claim type
- uncertainty
- Recorded
- 22 Mar 2026
- Publisher
- Lenny's Podcast
Transcript context
…That is such a good one because everyone's always just trying to acquire more resources, more investment, just like more features and showing that, "Okay, this is a terrible idea. I know I spent months on this, but no, we should kill this because it's not working." Right. It's not working. And here's how I'm going to know that it's not working. Here's when I'm going to come back to you with a decision. So sometimes we don't know that. Well, a lot of times we don't know the outcome, especially with AI native products. And if we can say, "We're going to test this. Here's how we're going to know it's working. We'll come back to you on X date." I think one thing that really spirals people out of control is a desire for certainty. As human beings, many of us have a huge desire for certainty. Now more than ever, that is not possible. And so one trick that I learned, especially working with engineers who often have a very, very high desire for certainty, is to say, "I don't know the answer right now. I don't know if this is going to be successful. I'm going to check in with you on X date. That's when we're going to come back and have another conversation." And so at least there's certainty about the next check-in point, and that can be a really powerful tool for deescalating the fears and risks around a given initiative or idea. Okay. Before we get into AI's impact and all this stuff, are there any other common mistakes people make when they are trying to get better at the skill of influence or just any other really powerful tactics for increasing your ability to influence leaders?…
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